Structure

Physi-Chem Properties

Molecular Weight:  524.15
Volume:  538.645
LogP:  5.468
LogD:  3.382
LogS:  -4.874
# Rotatable Bonds:  9
TPSA:  133.52
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.152
Synthetic Accessibility Score:  2.649
Fsp3:  0.032
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.245
MDCK Permeability:  9.33896535570966e-06
Pgp-inhibitor:  0.094
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.064
20% Bioavailability (F20%):  0.025
30% Bioavailability (F30%):  0.184

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  105.63591003417969%
Volume Distribution (VD):  0.201
Pgp-substrate:  0.2694154977798462%

ADMET: Metabolism

CYP1A2-inhibitor:  0.675
CYP1A2-substrate:  0.068
CYP2C19-inhibitor:  0.927
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.861
CYP2C9-substrate:  0.974
CYP2D6-inhibitor:  0.06
CYP2D6-substrate:  0.898
CYP3A4-inhibitor:  0.836
CYP3A4-substrate:  0.236

ADMET: Excretion

Clearance (CL):  8.429
Half-life (T1/2):  0.784

ADMET: Toxicity

hERG Blockers:  0.113
Human Hepatotoxicity (H-HT):  0.061
Drug-inuced Liver Injury (DILI):  0.899
AMES Toxicity:  0.86
Rat Oral Acute Toxicity:  0.304
Maximum Recommended Daily Dose:  0.922
Skin Sensitization:  0.959
Carcinogencity:  0.719
Eye Corrosion:  0.003
Eye Irritation:  0.938
Respiratory Toxicity:  0.117

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC190487

Natural Product ID:  NPC190487
Common Name*:   Rhuschalcone Iii
IUPAC Name:   (E)-1-(2,4-dihydroxyphenyl)-3-[4-[4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxyphenoxy]phenyl]prop-2-en-1-one
Synonyms:   rhuschalcone III
Standard InCHIKey:  VWFAAFDOTKTTKV-MKFXEVHTSA-N
Standard InCHI:  InChI=1S/C31H24O8/c1-38-30-18-29(37)25(27(35)15-7-19-2-8-21(32)9-3-19)17-31(30)39-23-11-4-20(5-12-23)6-14-26(34)24-13-10-22(33)16-28(24)36/h2-18,32-33,36-37H,1H3/b14-6+,15-7+
SMILES:  COc1cc(O)c(cc1Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1O)O)C(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL466790
PubChem CID:   5472698
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003472] 2'-Hydroxychalcones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32638 rhus pyroides Species Anacardiaceae Eukaryota root bark n.a. n.a. PMID[12762790]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT407 Cell Line COLO 205 Homo sapiens ED50 = 4.0 ug ml-1 PMID[480195]
NPT393 Cell Line HCT-116 Homo sapiens ED50 = 5.0 ug ml-1 PMID[480195]
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 4.0 ug ml-1 PMID[480195]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 3.0 ug ml-1 PMID[480195]
NPT386 Cell Line KM12 Homo sapiens ED50 = 4.0 ug ml-1 PMID[480195]
NPT323 Cell Line SW-620 Homo sapiens ED50 = 3.0 ug ml-1 PMID[480195]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 8933.05 nM PMID[480196]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 8810.49 nM PMID[480196]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 8749.84 nM PMID[480196]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 11066.24 nM PMID[480196]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 11350.11 nM PMID[480196]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 9484.18 nM PMID[480196]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 10162.49 nM PMID[480196]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 10423.17 nM PMID[480196]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 7362.07 nM PMID[480196]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 8892.01 nM PMID[480196]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 8375.29 nM PMID[480196]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 9749.9 nM PMID[480196]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 6934.26 nM PMID[480196]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 8072.35 nM PMID[480196]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 11324.0 nM PMID[480196]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 10069.32 nM PMID[480196]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 10789.47 nM PMID[480196]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 9015.71 nM PMID[480196]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 7979.95 nM PMID[480196]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 12852.87 nM PMID[480196]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 13740.42 nM PMID[480196]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 14962.36 nM PMID[480196]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 9794.9 nM PMID[480196]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 5011.87 nM PMID[480196]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 11246.05 nM PMID[480196]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 6745.28 nM PMID[480196]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 7413.1 nM PMID[480196]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 9616.12 nM PMID[480196]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10046.16 nM PMID[480196]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 6792.04 nM PMID[480196]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 8072.35 nM PMID[480196]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 8452.79 nM PMID[480196]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 8790.23 nM PMID[480196]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10092.53 nM PMID[480196]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 14825.18 nM PMID[480196]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 12618.28 nM PMID[480196]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 7852.36 nM PMID[480196]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 8851.16 nM PMID[480196]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 12971.79 nM PMID[480196]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 8810.49 nM PMID[480196]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 7211.07 nM PMID[480196]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 8689.6 nM PMID[480196]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 8356.03 nM PMID[480196]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 15275.66 nM PMID[480196]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 11614.49 nM PMID[480196]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 8609.94 nM PMID[480196]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 14157.94 nM PMID[480196]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10115.79 nM PMID[480196]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 8770.01 nM PMID[480196]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 7655.97 nM PMID[480196]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 8729.71 nM PMID[480196]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 14387.99 nM PMID[480196]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 10139.11 nM PMID[480196]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 7294.58 nM PMID[480196]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 7568.33 nM PMID[480196]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 8203.52 nM PMID[480196]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 8413.95 nM PMID[480196]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 8433.35 nM PMID[480196]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC190487 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC154304
0.9934 High Similarity NPC188967
0.9671 High Similarity NPC185526
0.9613 High Similarity NPC272064
0.9542 High Similarity NPC183
0.9484 High Similarity NPC34089
0.9484 High Similarity NPC196179
0.9474 High Similarity NPC472915
0.947 High Similarity NPC226973
0.947 High Similarity NPC208043
0.947 High Similarity NPC308451
0.9412 High Similarity NPC227325
0.9412 High Similarity NPC163780
0.9412 High Similarity NPC196439
0.9412 High Similarity NPC167815
0.9412 High Similarity NPC50715
0.9412 High Similarity NPC201136
0.9412 High Similarity NPC208197
0.9412 High Similarity NPC256612
0.9412 High Similarity NPC146165
0.9412 High Similarity NPC4455
0.9412 High Similarity NPC92659
0.9412 High Similarity NPC20830
0.9412 High Similarity NPC183597
0.9412 High Similarity NPC2476
0.9412 High Similarity NPC138360
0.9412 High Similarity NPC280339
0.9412 High Similarity NPC128863
0.9404 High Similarity NPC306821
0.9351 High Similarity NPC472916
0.9351 High Similarity NPC178854
0.9346 High Similarity NPC231018
0.9346 High Similarity NPC176775
0.9346 High Similarity NPC250822
0.9346 High Similarity NPC69394
0.9346 High Similarity NPC47781
0.9346 High Similarity NPC75279
0.9346 High Similarity NPC22519
0.9346 High Similarity NPC160951
0.9346 High Similarity NPC255350
0.9346 High Similarity NPC145379
0.9346 High Similarity NPC274327
0.9346 High Similarity NPC183878
0.9346 High Similarity NPC276409
0.9346 High Similarity NPC280937
0.9346 High Similarity NPC86485
0.9342 High Similarity NPC117579
0.9342 High Similarity NPC149614
0.9338 High Similarity NPC328119
0.9333 High Similarity NPC119660
0.9333 High Similarity NPC93034
0.9308 High Similarity NPC14662
0.9308 High Similarity NPC243877
0.929 High Similarity NPC476981
0.929 High Similarity NPC75215
0.929 High Similarity NPC189179
0.929 High Similarity NPC183851
0.929 High Similarity NPC112954
0.929 High Similarity NPC227192
0.929 High Similarity NPC63454
0.929 High Similarity NPC181960
0.929 High Similarity NPC224137
0.929 High Similarity NPC93376
0.9286 High Similarity NPC472909
0.9286 High Similarity NPC213622
0.9286 High Similarity NPC32557
0.9286 High Similarity NPC37392
0.9286 High Similarity NPC2928
0.9286 High Similarity NPC189960
0.9281 High Similarity NPC241498
0.9281 High Similarity NPC293183
0.9281 High Similarity NPC222830
0.9281 High Similarity NPC131624
0.9281 High Similarity NPC198826
0.9281 High Similarity NPC142540
0.9281 High Similarity NPC60972
0.9281 High Similarity NPC275722
0.9281 High Similarity NPC212678
0.9281 High Similarity NPC134677
0.9281 High Similarity NPC301323
0.9281 High Similarity NPC25270
0.9281 High Similarity NPC120163
0.9281 High Similarity NPC275836
0.9281 High Similarity NPC100887
0.9281 High Similarity NPC256283
0.9281 High Similarity NPC39732
0.9281 High Similarity NPC57030
0.9281 High Similarity NPC187498
0.9281 High Similarity NPC71334
0.9281 High Similarity NPC156222
0.9281 High Similarity NPC301123
0.9281 High Similarity NPC239128
0.9281 High Similarity NPC188203
0.9281 High Similarity NPC83508
0.9281 High Similarity NPC162313
0.9276 High Similarity NPC179183
0.9272 High Similarity NPC195202
0.9255 High Similarity NPC174700
0.925 High Similarity NPC280493
0.9231 High Similarity NPC105242
0.9231 High Similarity NPC9609
0.9231 High Similarity NPC115798
0.9231 High Similarity NPC284127
0.9231 High Similarity NPC25495
0.9231 High Similarity NPC172202
0.9231 High Similarity NPC261004
0.9231 High Similarity NPC191459
0.9231 High Similarity NPC143828
0.9231 High Similarity NPC176300
0.9231 High Similarity NPC18607
0.9231 High Similarity NPC19687
0.9231 High Similarity NPC476410
0.9231 High Similarity NPC4481
0.9231 High Similarity NPC22472
0.9231 High Similarity NPC288669
0.9231 High Similarity NPC204854
0.9231 High Similarity NPC130894
0.9231 High Similarity NPC193842
0.9231 High Similarity NPC7846
0.9231 High Similarity NPC18772
0.9231 High Similarity NPC300943
0.9231 High Similarity NPC152166
0.9231 High Similarity NPC253634
0.9226 High Similarity NPC49824
0.9226 High Similarity NPC98661
0.9226 High Similarity NPC474520
0.9226 High Similarity NPC247017
0.9221 High Similarity NPC206238
0.9221 High Similarity NPC292214
0.9221 High Similarity NPC271779
0.9221 High Similarity NPC167091
0.9221 High Similarity NPC246204
0.9221 High Similarity NPC88645
0.9216 High Similarity NPC262623
0.9211 High Similarity NPC102003
0.9211 High Similarity NPC92722
0.9205 High Similarity NPC62536
0.9205 High Similarity NPC205522
0.9205 High Similarity NPC33265
0.9205 High Similarity NPC12200
0.9205 High Similarity NPC85233
0.9187 High Similarity NPC295082
0.9182 High Similarity NPC477840
0.9177 High Similarity NPC83922
0.9177 High Similarity NPC472448
0.9177 High Similarity NPC477841
0.9177 High Similarity NPC219927
0.9172 High Similarity NPC476980
0.9167 High Similarity NPC78302
0.9167 High Similarity NPC29841
0.9167 High Similarity NPC110070
0.9167 High Similarity NPC287979
0.9167 High Similarity NPC7973
0.9167 High Similarity NPC470402
0.9167 High Similarity NPC176665
0.9167 High Similarity NPC96167
0.9167 High Similarity NPC472438
0.9167 High Similarity NPC235215
0.9167 High Similarity NPC101830
0.9167 High Similarity NPC472913
0.9167 High Similarity NPC474208
0.9167 High Similarity NPC163524
0.9167 High Similarity NPC474836
0.9167 High Similarity NPC99597
0.9167 High Similarity NPC472914
0.9167 High Similarity NPC203891
0.9167 High Similarity NPC472911
0.9167 High Similarity NPC162869
0.9167 High Similarity NPC48208
0.9167 High Similarity NPC156057
0.9167 High Similarity NPC245758
0.9167 High Similarity NPC210084
0.9167 High Similarity NPC475267
0.9167 High Similarity NPC262286
0.9167 High Similarity NPC36852
0.9167 High Similarity NPC222814
0.9167 High Similarity NPC472910
0.9167 High Similarity NPC78225
0.9167 High Similarity NPC305663
0.9161 High Similarity NPC44079
0.9161 High Similarity NPC201451
0.9161 High Similarity NPC31018
0.9161 High Similarity NPC255807
0.9161 High Similarity NPC26227
0.9156 High Similarity NPC257648
0.9156 High Similarity NPC161277
0.9156 High Similarity NPC101996
0.9156 High Similarity NPC199100
0.9156 High Similarity NPC180234
0.9156 High Similarity NPC477231
0.9156 High Similarity NPC39007
0.9156 High Similarity NPC120537
0.915 High Similarity NPC219330
0.915 High Similarity NPC184136
0.915 High Similarity NPC45873
0.915 High Similarity NPC156953
0.915 High Similarity NPC166753
0.915 High Similarity NPC239363
0.915 High Similarity NPC50728
0.9145 High Similarity NPC10304

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC190487 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9346 High Similarity NPD2801 Approved
0.8944 High Similarity NPD6168 Clinical (unspecified phase)
0.8944 High Similarity NPD6166 Phase 2
0.8944 High Similarity NPD6167 Clinical (unspecified phase)
0.891 High Similarity NPD1934 Approved
0.8861 High Similarity NPD3882 Suspended
0.8758 High Similarity NPD1511 Approved
0.8742 High Similarity NPD4868 Clinical (unspecified phase)
0.8734 High Similarity NPD2393 Clinical (unspecified phase)
0.8696 High Similarity NPD5494 Approved
0.8679 High Similarity NPD3817 Phase 2
0.8645 High Similarity NPD1512 Approved
0.8606 High Similarity NPD3818 Discontinued
0.8589 High Similarity NPD6232 Discontinued
0.8581 High Similarity NPD7410 Clinical (unspecified phase)
0.8571 High Similarity NPD4338 Clinical (unspecified phase)
0.8554 High Similarity NPD7054 Approved
0.8545 High Similarity NPD7473 Discontinued
0.8503 High Similarity NPD7472 Approved
0.8503 High Similarity NPD7074 Phase 3
0.8462 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD5844 Phase 1
0.8428 Intermediate Similarity NPD4380 Phase 2
0.8415 Intermediate Similarity NPD6959 Discontinued
0.8375 Intermediate Similarity NPD7411 Suspended
0.8353 Intermediate Similarity NPD7808 Phase 3
0.8344 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD6797 Phase 2
0.8333 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD5402 Approved
0.8312 Intermediate Similarity NPD1549 Phase 2
0.8294 Intermediate Similarity NPD7251 Discontinued
0.8263 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD1510 Phase 2
0.8232 Intermediate Similarity NPD7075 Discontinued
0.8212 Intermediate Similarity NPD1240 Approved
0.8204 Intermediate Similarity NPD3926 Phase 2
0.8182 Intermediate Similarity NPD2796 Approved
0.8171 Intermediate Similarity NPD7768 Phase 2
0.8165 Intermediate Similarity NPD6799 Approved
0.816 Intermediate Similarity NPD1465 Phase 2
0.816 Intermediate Similarity NPD7819 Suspended
0.8125 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD3749 Approved
0.8105 Intermediate Similarity NPD1607 Approved
0.8084 Intermediate Similarity NPD1247 Approved
0.8068 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD6801 Discontinued
0.7974 Intermediate Similarity NPD943 Approved
0.7949 Intermediate Similarity NPD2935 Discontinued
0.7922 Intermediate Similarity NPD447 Suspended
0.7907 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD5403 Approved
0.7874 Intermediate Similarity NPD6559 Discontinued
0.7866 Intermediate Similarity NPD6599 Discontinued
0.7862 Intermediate Similarity NPD3750 Approved
0.7848 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD7390 Discontinued
0.7799 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5401 Approved
0.7751 Intermediate Similarity NPD919 Approved
0.7722 Intermediate Similarity NPD1551 Phase 2
0.7716 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD3226 Approved
0.7692 Intermediate Similarity NPD230 Phase 1
0.7688 Intermediate Similarity NPD2800 Approved
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD2344 Approved
0.7661 Intermediate Similarity NPD7199 Phase 2
0.7644 Intermediate Similarity NPD3751 Discontinued
0.7616 Intermediate Similarity NPD3787 Discontinued
0.7613 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD6190 Approved
0.7584 Intermediate Similarity NPD8312 Approved
0.7584 Intermediate Similarity NPD8313 Approved
0.7581 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD1933 Approved
0.7572 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD2534 Approved
0.7561 Intermediate Similarity NPD2532 Approved
0.7561 Intermediate Similarity NPD2533 Approved
0.7547 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD3748 Approved
0.7547 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD1653 Approved
0.7516 Intermediate Similarity NPD1613 Approved
0.7516 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5953 Discontinued
0.75 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2309 Approved
0.7484 Intermediate Similarity NPD4908 Phase 1
0.747 Intermediate Similarity NPD920 Approved
0.7456 Intermediate Similarity NPD37 Approved
0.7455 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD6234 Discontinued
0.7438 Intermediate Similarity NPD2799 Discontinued
0.7436 Intermediate Similarity NPD3027 Phase 3
0.7427 Intermediate Similarity NPD4966 Approved
0.7427 Intermediate Similarity NPD4965 Approved
0.7427 Intermediate Similarity NPD4967 Phase 2
0.7423 Intermediate Similarity NPD4628 Phase 3
0.7421 Intermediate Similarity NPD6651 Approved
0.7419 Intermediate Similarity NPD9494 Approved
0.7403 Intermediate Similarity NPD1203 Approved
0.7401 Intermediate Similarity NPD7286 Phase 2
0.7394 Intermediate Similarity NPD6776 Approved
0.7394 Intermediate Similarity NPD6780 Approved
0.7394 Intermediate Similarity NPD6779 Approved
0.7394 Intermediate Similarity NPD6777 Approved
0.7394 Intermediate Similarity NPD6781 Approved
0.7394 Intermediate Similarity NPD6778 Approved
0.7394 Intermediate Similarity NPD6782 Approved
0.7391 Intermediate Similarity NPD6100 Approved
0.7391 Intermediate Similarity NPD6099 Approved
0.7389 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD2313 Discontinued
0.7386 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6832 Phase 2
0.7362 Intermediate Similarity NPD1243 Approved
0.7353 Intermediate Similarity NPD6844 Discontinued
0.7349 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2346 Discontinued
0.733 Intermediate Similarity NPD7870 Phase 2
0.733 Intermediate Similarity NPD7871 Phase 2
0.7326 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD5406 Approved
0.7284 Intermediate Similarity NPD5408 Approved
0.7284 Intermediate Similarity NPD5404 Approved
0.7284 Intermediate Similarity NPD5405 Approved
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7277 Intermediate Similarity NPD7696 Phase 3
0.7277 Intermediate Similarity NPD7697 Approved
0.7277 Intermediate Similarity NPD7435 Discontinued
0.7277 Intermediate Similarity NPD7698 Approved
0.7273 Intermediate Similarity NPD5242 Approved
0.7268 Intermediate Similarity NPD8151 Discontinued
0.725 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD7228 Approved
0.7246 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7549 Discontinued
0.7238 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6233 Phase 2
0.7229 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD9717 Approved
0.7197 Intermediate Similarity NPD3018 Phase 2
0.7193 Intermediate Similarity NPD6386 Approved
0.7193 Intermediate Similarity NPD6385 Approved
0.7189 Intermediate Similarity NPD4287 Approved
0.7186 Intermediate Similarity NPD4357 Discontinued
0.7176 Intermediate Similarity NPD7458 Discontinued
0.7174 Intermediate Similarity NPD8434 Phase 2
0.7174 Intermediate Similarity NPD8150 Discontinued
0.7168 Intermediate Similarity NPD5353 Approved
0.7159 Intermediate Similarity NPD8127 Discontinued
0.7152 Intermediate Similarity NPD5536 Phase 2
0.7143 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6823 Phase 2
0.7134 Intermediate Similarity NPD2798 Approved
0.7128 Intermediate Similarity NPD6535 Approved
0.7128 Intermediate Similarity NPD7701 Phase 2
0.7128 Intermediate Similarity NPD6534 Approved
0.7119 Intermediate Similarity NPD7229 Phase 3
0.711 Intermediate Similarity NPD8455 Phase 2
0.7107 Intermediate Similarity NPD7783 Phase 2
0.7107 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1548 Phase 1
0.7097 Intermediate Similarity NPD9269 Phase 2
0.7088 Intermediate Similarity NPD7038 Approved
0.7088 Intermediate Similarity NPD7039 Approved
0.7086 Intermediate Similarity NPD6971 Discontinued
0.7076 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD1470 Approved
0.7063 Intermediate Similarity NPD411 Approved
0.7063 Intermediate Similarity NPD3764 Approved
0.7063 Intermediate Similarity NPD3268 Approved
0.7063 Intermediate Similarity NPD6798 Discontinued
0.7059 Intermediate Similarity NPD9268 Approved
0.7056 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7874 Approved
0.7056 Intermediate Similarity NPD7177 Discontinued
0.7051 Intermediate Similarity NPD2982 Phase 2
0.7051 Intermediate Similarity NPD2983 Phase 2
0.7048 Intermediate Similarity NPD2654 Approved
0.7039 Intermediate Similarity NPD2403 Approved
0.7039 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4360 Phase 2
0.7037 Intermediate Similarity NPD4363 Phase 3
0.7032 Intermediate Similarity NPD422 Phase 1
0.7032 Intermediate Similarity NPD1610 Phase 2
0.7022 Intermediate Similarity NPD5710 Approved
0.7022 Intermediate Similarity NPD5711 Approved
0.702 Intermediate Similarity NPD7801 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data